If you haven’t dated in a while, or have found yourself recently out of a long-term relationship, reentering the dating world can be a fearsome task – it’s all too easy to second guess just about everything you’re saying and doing while making a first impression.
Personally, I've found that first dates go south a hell of a lot more often because one person is trying to hard to be impressive than because of sheer incompatibility. On the opposite side of the coin, though, “just be yourself” is a certifiably horrendous piece of advice, because most of the time, it gives license to avoid placing any effort into the experience at all.
The best guidance to be given here is simple if you consider that most men and women arrive at a first date looking for friendliness, consideration, and authenticity before they even think about confidence or chemistry. If you’re able to show another person your best qualities while hitting on those points, you’re likely headed for a second date unless your personalities clash in an irreconcilable way.
Pick the Right Spot
The specific location choice doesn’t matter as much as the connection you build while you’re there, but when you’re choosing a locale to spend your first few hours together, try to at least make the choice cooperatively or propose a venue where you’re positive your date will feel comfortable and relaxed. The only other real rule to go by here it to make sure you’ve chosen a setting that’s conducive to building a rapport. A small, quiet cocktail bar is great, for example. A packed-to-the-walls dive with loud music, not so much.
While rambling on about your prestigious degree or focusing on your latest accomplishment at the office might make you feel more impressive, that’s an easy way to come off as arrogant. While you’re getting to know someone new, try your best to leave your qualifications at the door and focus on talking about what really matters to you and what you’re passionate about Ask questions. Show you’re legitimately interested in the answers by asking follow-ups and pointing out when you find common ground on a topic or past experience. And when you talk about yourself, stick to the whole truth. Don't exaggerate and don't hide – just be open.
There’s nothing that can make a new person in your life feel special like a healthy dose of thoughtfulness. Ask your date for his or her opinions and feelings, and remembering details and bringing them up in conversation later are all great ways to start. In my experience, though, thoughtfulness is best shown through small favors or gestures. For example, if your date mentions that he or she loves a good slice of cheesecake, and you know of a great bakery nearby, take ‘em there and pick up a slice to split. Or, if your date mentions that they’ve had a tough day, give them some time to vent before you try to change the subject. Bottom line, if you’re showing that you’re willing to put conscious effort into making your date happier and more comfortable, they’ll seriously appreciate it.
This one might seem a bit obvious, but I’ve met a ton of perfectly nice guys who’ve tried to suppress their nice side for fear of coming across as a pushover. While nobody wants to date a doormat, most people actively want to be with someone who treats them well and isn’t afraid of vulnerability. Being as kind as possible while showing that you highly value yourself is a huge leg up in the dating world.
Remember, though, kindness isn’t about performing excessive favors or putting a ton of effort into looking chivalrous because you feel you need to. By this, I mean that if you’d like to pay for dinner or go out of the way to hold open every door you pass, don’t do it because you think it’s what a guy should do, do it because you want to show your date that you care about treating them nicely. Just don’t go overboard.
Make sure your body language is relaxed and approachable, smile often, make eye contact, and don't be afraid to crack a joke now again to keep things light and entertaining. That's it. With luck, you'll make your date feel comfortable and confident while you get to know each other. I’ve found that being consciously affectionate works wonders, too. That doesn't mean trying to get handsy – it means offering honest compliments when they’re warranted and speaking about the best people in your life in a loving, warm-hearted way to show that you’re proud and comfortable expressing your emotions. Which will, hopefully, in turn, make your date feel more secure in expressing their own.
It can be terrifying, I know. But vulnerability, honesty, and authenticity will always win when you’re trying to get to know someone new. No matter how long you’ve been off the market or how anxious you may feel interacting with someone new, showing off the most genuine and thoughtful sides of yourself is a great way to put your best foot forward — and really, that's all you can do.